A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Pool

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (320 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is €89
includes taxes & fees
6 Jul - 7 Jul
Clinton Motel
Lobby

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is €119
includes taxes & fees
26 Jul - 27 Jul
Quality Inn Old Saybrook - Westbrook
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (482 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is €81
includes taxes & fees
12 Jul - 13 Jul
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Pristine waters await at this coastal retreat with private beach access and year-round pools.
The price is €319
includes taxes & fees
12 Jul - 13 Jul
Water's Edge Resort & Spa
Indoor pool, outdoor pool

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
The price is €271
includes taxes & fees
7 Jul - 8 Jul
Hyatt Place Long Island East End
Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,005 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is €423
includes taxes & fees
6 Jul - 7 Jul
Saybrook Point Resort & Marina
Indoor pool, seasonal outdoor pool, pool loungers

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (818 reviews)
  • cleanliness
    Plunge into seaside bliss at a beachfront haven with private white sands, seasonal outdoor pool, and indoor swimming sanctuary.
The price is €1,319
includes taxes & fees
8 Jul - 9 Jul
Gurney's Montauk Resort & Seawater Spa
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is €718
includes taxes & fees
6 Jul - 7 Jul
The Pridwin Hotel
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (152 reviews)
  • cleanliness
    Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
The price is €2,786
includes taxes & fees
7 Jul - 8 Jul
Topping Rose House
Seasonal outdoor pool

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.8 out of 10, (828 reviews)
  • cleanliness
    Escape summer heat at this serene riverfront motel with a clean, seasonal pool.
The price is €125
includes taxes & fees
7 Jul - 8 Jul
Budget Host East End
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"V"
Liliana 2-night trip
Posted 2 days ago
Ocean Surf Resort

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Manor: Features sunloungers, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Shelter Island?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as Sunset Beach and Shelter Island Whale's Tail.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.